6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose | 289665-46-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose
• 英文别名: 2-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-(4-methylphenyl)sulfonyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethyl benzoate
• CAS: 289665-46-9
• 化学式: C₂₃H₂₆O₈S
• 分子量: 462.521
• InChiKey: NLTJKCYLBQGSHA-XAPVIXHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose 在 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 97.0h， 生成 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol
  参考文献：
  名称：

  Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol

  摘要：

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00136-1
• 作为产物：
  描述：

  1,2-O-isopropylidene-3β-O-tosyl-α-D-glucofuranose 在 吡啶 、 dimethyl sulfide borane 、 乙酸酐 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 6-benzoyl-1,2-O-isopropylidene-3-O-tosyl-5-deoxy-α-D-glucofuranose
  参考文献：
  名称：

  Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol

  摘要：

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00136-1

文献信息

• Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol
  作者：X.B Tian、J.M Min、L.H Zhang

  DOI：10.1016/s0957-4166(00)00136-1

  日期：2000.5

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.